Methyl anisate → 4-Methoxy-3-(2-methyl-benzoyl)-benzoic acid methyl ester

HRID 521502

반응식

HRID 521502 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[CH3:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].[Sn](Cl)(Cl)(Cl)Cl>ClC1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[CH3:13])[CH:5]=1

참가 물질

5

반응물 3

HCID 8499Methyl anisateHCID 24287Tin tetrachloride2회HCID 702762-Methylbenzoyl chloride

생성물 1

HCID 670766294-Methoxy-3-(2-methyl-benzoyl)-benzoic acid methyl ester수율 2.3%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

반응 조건

온도
140 °C

실험 절차

4-Methoxybenzoic acid methyl ester (5.00 g, 30.1 mmol) and 2-methylbenzoyl chloride (4.88 g, 31.6 mmol) were dissolved in chlorobenzene (10 ml), tin(IV) chloride (9.41 g, 36.1 mmol) was added cautiously, and the mixture was heated to 140° C. for 3 h. The addition of the acid chloride and tin tetrachloride was repeated twice, and the mixture subsequently heated to 140° C. for 3 h each time. The mixture was poured onto 300 ml of ice/water and extracted with DCM. The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) and subsequently by RP HPLC (water/ACN gradient) to yield 200 mg of the title compound.

후처리

  1. temperaturethe mixture subsequently heated to 140° C. for 3 h each time
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel chromatography (HEP/EA gradient) and subsequently by RP HPLC (water/ACN gradient)

출처 및 근거

ORD 기록
ord-25f12cb9926942ddae7c60be553fed9d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328071B2

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